This article explores literacy sponsorship at an early 19th-century academy that schooled young Native American men near Lexington, Kentucky. In doing so, it presents two case studies based on the correspondence of J. N. Bourassa (Potawatomi) and Adam Nail (Choctaw), both advanced students at the academy who turned their literacy lessons toward a critique of their living and learning conditions. In examining their letters to federal authorities, it is possible to discern how the students moved beyond the limited literacy sponsored by the academy to embrace liberatory practices reserved by the White elites who managed the institution.